WO1987007622A1 - Copolymere homogenes thermodurcissables - Google Patents

Copolymere homogenes thermodurcissables Download PDF

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Publication number
WO1987007622A1
WO1987007622A1 PCT/US1987/001053 US8701053W WO8707622A1 WO 1987007622 A1 WO1987007622 A1 WO 1987007622A1 US 8701053 W US8701053 W US 8701053W WO 8707622 A1 WO8707622 A1 WO 8707622A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyphenol
copolymer
group
set forth
vinyl benzyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1987/001053
Other languages
English (en)
Inventor
William Daniel Varnell
Thomas Dean Newton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Allied Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Allied Corp filed Critical Allied Corp
Priority to FI880541A priority Critical patent/FI880541A0/fi
Priority to KR1019880700131A priority patent/KR880701258A/ko
Priority to AU12905/88A priority patent/AU1290588A/en
Priority to PCT/US1987/003368 priority patent/WO1988007562A1/fr
Priority to EP19880901514 priority patent/EP0307420A1/fr
Priority to FI885402A priority patent/FI885402L/fi
Publication of WO1987007622A1 publication Critical patent/WO1987007622A1/fr
Priority to NO880367A priority patent/NO171369C/no
Priority to DK60788A priority patent/DK60788A/da
Priority to DK653888A priority patent/DK653888D0/da
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0326—Organic insulating material consisting of one material containing O
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]

Definitions

  • circuit boards which are used in relatively complicated pieces of equipment such as main frame computers, must be of a relatively high standard of quality in order to function in an efficient manner for a long period of time without deteriorating or breaking down, and thus causing an interruption in the function of the machine.
  • This high quality of material is opposed to pieces of equipment requiring a lower standard of quality such as those used in personal computers, high quality television equipment, radios, etc.
  • Circuit boards upon which a circuit is etched or implanted usually comprise a -laminate which is composed of a synthetic polymeric substance which possesses desirable characteristics such as thermal stability, low coefficient of thermal expansion, dimensional stability, low dielectric constant, solvent resistance, low moisture absorption, etc. and a suitable reinforcement matrix, such as glass, quartz, graphite, Kevlar, ( ' etc.
  • a homogeneous thermoset copolymer of a vinyl benzyl terminated ether of a polyphenol and a dicyanate ester of a polyether of a polyphenol may be used in the preparation of laminates which themselves will form a component of a circuit board and will possess the desirable characteristics hereinbefore set forth.
  • thermoset copolymers More specifically, the invention is concerned with novel high temperature homogeneous thermoset copolymers and to a method for the preparation thereof.
  • the homogeneous thermoset copolymers of the pre-sent invention which constitute novel compositions.of matter, may be used to coat and/or impregnate a substrate which is thereafter cured and utilized in circuit board laminates and dielectric coatings, the use thereof being attributable to the desirable characteristics which are possessed by these polymeric compositions of matter.
  • the particular characteristics of the polymer dielectric and reinforcing components which go to make up the circuit boards contribute to the efficiency and stability of the final electronic equipment in which the circuit boards are used.
  • the polymeric matrix of the present invention possesses a lower dielectric constant than that which is possessed by ther osetting polyimide or ep ⁇ xy matrices which are used as the standards by the industry for electrical laminates.
  • thermoset copolymers It is therefore an object of this invention to provide novel homogeneous thermoset copolymers.
  • Another object of this invention is to provide a method for preparing h ⁇ nogeneous thermoset copolymers which are useful as a component in circuit board laminates.
  • an embodiment of this invention resides in a homogeneous thermoset copolymer of 1) a vinyl benzyl terminated ether of a polyphenol having the structure:
  • X is selected from the group consisting of CH3-C-CH3, S02, 0, S and CH2 radicals
  • R is selected from the group consisting of -CH2-C6H4-CH2-, (CH2)b in which b ranges from 1 to about 6, - ⁇ _H2- ⁇ _-H»CH-CH2- and -CH2-0 « -CH2- radicals
  • A is independently selected frcm the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alk ⁇ xy and phenyl radicals and n has an average value in the range of from about 0 to about 20, and 2 ⁇ a dicyanate ester of a polyphenol having the structure:
  • X is selected from the group consisting of CH3-OC ⁇ 3, S02, 0, S and CH2 radicals
  • R is selected from the group consisting of -CH2-C6H4-CH2-, (CH2)b in which b ranges from 1 to about 6, -CH2-CHs H-CH2- and -CH2-OC-CH2- radicals
  • B is independently selected frcm the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alk ⁇ xy and phenyl radicals and m has an average value in the range of from about 0 to about 20.
  • X is selected from the group consisting of CH3-C-CH3, S02, 0, S and CH2 radicals
  • R is selected from the group consisting of -CH2-C6H4-CH2-, (CH2)b in which b ranges from 1 to about 6, -CH2-CE CH-CH2- and -CH2-O -CH2- radicals
  • A is independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alkoxy and phenyl radicals and n has an average value in the range of from about 0 to about 20 with a dicyanate ester of a polyphenol having the structure:
  • X is selected from the group consisting of CH3-C-CH3, S02, 0, S and CH2 radicals
  • B is independently selected frcm the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alk ⁇ xy and phenyl radicals and m has an average value
  • thermoset copolymer in the range of from about 0 to about 20 at reaction conditions, and recovering the resultant homogeneous thermoset copolymer.
  • the present invention is concerned with novel homogeneous thermoset copolymers and to a method for the preparation of these copolymers.
  • the homogeneous thermoset copolymers will comprise a mixture of a vinyl benzyl terminated ether of a polyphenol and a dicyanate ester of a polyphenol, examples of these compounds being hereinafter set forth in greater detail.
  • the copolymerization of these compounds will result in a copolymer which, because of its particular structure, will be useful in electronic circuitry, said composite possessing a relatively low dielectric constant and a high glass transition temperature, these characteristics being of particular advantage for use in circuit boards.
  • the vinyl benzyl terminated ether of a polyphenol which forms the first component of the copolymer of the present invention will possess the generic structure :
  • X is selected from the group consisting of CH3-C-CH3, 902, 0, S and CH2 radicals
  • R is selected from the group consisting of -CH2-C6H4-CH2-, (CH2)b in which b ranges from 1 to about 6, -CH2-CBX-EK2E- and -CH2-OC-CH2- radicals
  • A is independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alk ⁇ xy and phenyl radicals and n has an average value in the range of from about 0 to about 20. Specific examples of this first component are given by the following chemical structures:
  • the second component of the copolymer of the present invention will comprise a dicyanate ester of a polyphenol which possesses the generic structure:
  • X is selected from the group consisting of CH3-C-CH3, S02, 0, S and CH2 radicals
  • R is selected from the group consisting of -CH2-C6H4-CH2-, (CH2)b in which b ranges from 1 to about 6, -CH2-CH ⁇ H-CH2- and -CH2-OC-CH2- radicals
  • B is independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine, alkyl, alkcxy and phenyl radicals and m has an average value in the range of frcm about 0 to about 20.
  • this second component is given by the following chemical structure:
  • novel homogeneous thermoset copolymers of the present invention may be prepared in any suitable manner of operation which is. known in the art.
  • one method of preparing the copolymer is to blend the two components hereinbefore described to form a hcmogeneous melt, said blending being effected at a temperature in the range of from about 100° to about 200%.
  • the homogeneous melt may then be poured into a mold or utilized in other various ways such as encapsulating a chip, and cured at an elevated temperature in the range of from about 150° to about 200°C and at a pressure of from atmospheric to about 50 atmospheres for a period of time which may range from about 0.1 to about 1 hour, and thereafter may be post-cured at a temperature ranging from about 200° to about 260°C for a period of time which may range from about 1 to about 12 hours in duration.
  • another method of preparing the desired copolymer of the present invention is to dissolve the vinyl benzyl terminated ether of a polyphenol and the dicyanate ester of a polyphenol in an appropriate solvent such as dimethyl formamide, N-methylpyrrolidinone, dimethyl aceta ⁇ dde, acetone, benzene, toluene, etc., in " amounts so that the resulting solution will contain from about 30 to about 70% by weight of the components of the copolymer.
  • an appropriate solvent such as dimethyl formamide, N-methylpyrrolidinone, dimethyl aceta ⁇ dde, acetone, benzene, toluene, etc.
  • the resulting solution may then be coated and/or impregnated on an appropriate substrate such as various resins, glass cloth, etc., and treated at an elevated temperature of from about 150° to about 180°c for a relatively short period of time, which may range frcm about 1 to about 10 minutes, to obtain a prepreg.
  • the resulting prepreg may then be stacked by pressing a predetermined number of sheets of the prepreg and pressing the stack in a heated press to form a desired laminate.
  • the pressing of the prepreg may be effected for a period of time ranging from about 1 to about 4 hours in duration at an elevated temperature ranging from about 150 to about 190°C, at a pressure in the range of from about 500 to about 1,000 psig (3448 to
  • the laminate is then subjected to a post-cure which is effected at a temperature in the range of from about 200° to about 260°C for a period of time which may range from about 3 to about 6 hours in duration.
  • a post-cure which is effected at a temperature in the range of from about 200° to about 260°C for a period of time which may range from about 3 to about 6 hours in duration.
  • the homogeneous thermoset copolymers may be prepared in a continuous manner of operation. When this type of operation is employed, the predetermined amounts of the vinyl benzyl terminated ether of a polyphenol and the dicyanate ester of a polyphenol which have been dissolved in an appropriate solvent of the type hereinbefore set forth in greater detail , are continuously charged to a zone which is maintained at the proper operating conditions of temperature and pressure.
  • thermoset copolymers a continuous reactant charge is necessary, with amounts depending upon the individual components, to provide a high yield of product which contains the desired percentage of each component in the finished h ⁇ nogeneous thermoset copolymers.
  • the mixture resulting therefrom may be continuously withdrawn and utilized to coat andor impregnate a substrate or reinforcement.
  • the coated or impregnated substrate or reinforcement may thereafter be continuously charged to a curing zone where it is subjected to a partial cure by passage through this zone which is maintained at varying operating temperatures for a predetermined period of time. After passage through the zone, the resulting prepreg material is continuously withdrawn and passed to storage.
  • the prepreg can then be layed up as sheets with or without a metal such as copper foil as an electrical or thermal conductor, and pressed in a predetermined number of sheets to form the desired laminate or circuit board matrix.
  • the circuit board precursor may be prepared by a solventless continuation lamination process.
  • the solid resin blend comprising at least one vinyl benzyl terminated ether of a polyphenol and a dicyanate ester of a polyphenol is used to impregnate a reinforcement such as glass cloth which is continuously fed through an appropriate apparatus.
  • the reinforcement such as the glass cloth may pass through this apparatus in a single ply or, if so desired, in a predetermined number of plies, one criteria being that each ply is impregnated with the resin blend.
  • the laminate is also contemplated that, if the laminate is to be used as a circuit board, one or both sides of the laminate may be covered with a metallic coating such as copper foil.
  • the laminate is then passed through the apparatus under predetermined conditions of temperature and pressure so as to provide a finished and cured laminate which emerges from the apparatus. This metal-covered laminate or uncovered laminate may then be cut into desired sizes and utilized, as hereinbefore set forth, as a circuit board in various electric or electronic devices.
  • the two components of the final ccmposition of matter may be present in various weight ratios.
  • the vinyl benzyl terminated ether of a polyphenol will be present in the finished composite in an amount in the range of from about 10% to about 90% by weight of the finished composite, while conversely the dicyanate ester of a polyphenol will be present in an amount in the range of from about 90% to about 10% by weight of the composite. While these weight ratios are preferred, it is also contemplated within the scope of this invention that either of the two components may be present in the finished composite in either a greater amount or a lesser amount, depending upon the particular properties which are desired to be possessed by the finished composite.
  • thermoset copolymers of the present invention In addition to the aforementioned favorable characteristics which are possessed by the homogeneous thermoset copolymers of the present invention, another advantage in utilizing these copolymers as components of a laminate is realized by employing a halogenated derivative of the vinylbenzyl terminated ether of a polyphenol or the dicyanate ester of a polyphenol as a component of the copolymer.
  • a halogenated derivative of the vinylbenzyl terminated ether of a polyphenol or the dicyanate ester of a polyphenol as a component of the copolymer.
  • the presence of these halogenated derivatives, and especially the brc ⁇ nated or chlorinated derivative will introduce a desired property enhancement to a substrate or reinforcement in that the laminate may then meet certain fla ⁇ mability requirements such as UL 94 flaamability tests.
  • thermoset copolymers of the present invention which possess the aforementioned desirable properties and to a method for the preparation thereof.
  • these examples are given merely for purposes of illustration and that the present invention is not necessarily limited thereto.
  • thermoset copolymer 21.9 grams of vinyl benzyl capped polyphenol of the following structure:
  • the prepreg was then pressed at a temperature of 1779c and a pressure of 200 p ⁇ ig (.379 kPa gage) for a period of 1 hour to form a laminate.
  • This laminate was then post-cured at a temperature of 230°c for a period of three hours. Analysis of the post-cured laminate by DSC showed a Tg of greater than 240 C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Reinforced Plastic Materials (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Laminated Bodies (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Les nouvelles compositions décrites comprennent des copolymères homogènes thermodurcissables résultant de la réaction entre un éther à terminaison vinyl-benzyle d'un polyphénol et un ester de dicyanate d'un polyphénol. Lesdites compositions peuvent être utilisées comme constituants de stratifiés employés dans des cartes de circuits électroniques. Lesdits copolymères permettent au produit fini de présenter les caractéristiques désirées, telles que des températures élevées de transition vitreuse et des constantes diélectriques basses.
PCT/US1987/001053 1986-06-06 1987-05-07 Copolymere homogenes thermodurcissables Ceased WO1987007622A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
FI880541A FI880541A0 (fi) 1986-06-06 1987-05-07 Homogena haordplastkopolymerer.
KR1019880700131A KR880701258A (ko) 1986-06-06 1987-05-07 균질환 열경화성 공중합체
FI885402A FI885402L (fi) 1987-03-23 1987-12-17 Homogena, i hetta haerdbara kopolymerer.
PCT/US1987/003368 WO1988007562A1 (fr) 1987-03-23 1987-12-17 Copolymeres thermodurcis homogenes
EP19880901514 EP0307420A1 (fr) 1987-03-23 1987-12-17 Copolymeres thermodurcis homogenes
AU12905/88A AU1290588A (en) 1987-03-23 1987-12-17 Homogeneous thermoset copolymers
NO880367A NO171369C (no) 1986-06-06 1988-01-28 Homogene varmherdende copolymerer og fremgangsmaate for fremstilling av slike
DK60788A DK60788A (da) 1986-06-06 1988-02-05 Homogen, varmehaerdet copolymer og fremgangsmaade til dens fremstilling
DK653888A DK653888D0 (da) 1987-03-23 1988-11-23 Homogene, termohaerdende copolymerer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/871,337 US4665154A (en) 1986-06-06 1986-06-06 Homogeneous thermoset copolymer from poly (vinyl benzyl ether) and dicyanate ester
US871,337 1986-06-06

Publications (1)

Publication Number Publication Date
WO1987007622A1 true WO1987007622A1 (fr) 1987-12-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1987/001053 Ceased WO1987007622A1 (fr) 1986-06-06 1987-05-07 Copolymere homogenes thermodurcissables

Country Status (10)

Country Link
US (1) US4665154A (fr)
EP (1) EP0270601A1 (fr)
JP (1) JPH01501156A (fr)
KR (1) KR880701258A (fr)
AU (1) AU592192B2 (fr)
CA (1) CA1274045A (fr)
DK (1) DK60788A (fr)
ES (1) ES2005870A6 (fr)
FI (1) FI880541A0 (fr)
WO (1) WO1987007622A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0373784A3 (fr) * 1988-12-12 1992-01-22 Imperial Chemical Industries Plc Polymère aromatique

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4777226A (en) * 1986-06-12 1988-10-11 Allied Corporation Terpolymer from (1) a poly(vinylbenzylether) of a polyphenol (2) a cyanate ester of a polyphenol and (3) alkenyl aryl compound
US4782116A (en) * 1986-07-21 1988-11-01 Allied-Signal Inc. Homogeneous thermoset terpolymers
US4873302A (en) * 1986-08-11 1989-10-10 Allied-Signal Inc. Styrene-terminated polyethers of polyphenols
US4774316A (en) * 1986-08-15 1988-09-27 The Dow Chemical Company Copolymer of vinylbenzyl ether of polyhydric halogenated phenolic compound and aromatic polycyanate ester compound
US4740584A (en) * 1986-09-08 1988-04-26 Interez, Inc. Blend of dicyanate esters of dihydric phenols
US4940848A (en) * 1987-05-04 1990-07-10 Hi-Tek Polymers, Inc. Stable solutions of prepolymers of thiodi(phenylcyanate) and laminating method employing same
EP0382751B1 (fr) * 1987-08-21 1994-03-02 AlliedSignal Inc. Phenols olygomeres multifonctionnels a terminaison styrene utiles en tant que nouvelles resines a thermoprise pour composites
US5428125A (en) * 1989-07-17 1995-06-27 The Dow Chemical Company Mesogenic polycyanates and thermosets thereof
US5442039A (en) * 1989-07-17 1995-08-15 The Dow Chemical Company Mesogenic polycyanates and thermosets thereof
US5260398A (en) * 1990-04-05 1993-11-09 The Dow Chemical Company Aromatic cyanate-siloxane
US5206321A (en) * 1991-10-03 1993-04-27 The Dow Chemical Company Polycyanates containing mesogenic moieties as lateral substituents
JP4570417B2 (ja) * 2004-08-06 2010-10-27 ナミックス株式会社 液状の封止用樹脂組成物
CN104718426A (zh) 2012-10-12 2015-06-17 帝斯曼知识产权资产管理有限公司 复合防弹雷达罩壁及其制造方法
US10153546B2 (en) 2013-07-02 2018-12-11 Dsm Ip Assets B.V. Composite antiballistic radome walls and methods of making the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4116946A (en) * 1976-06-24 1978-09-26 Bayer Aktiengesellschaft Hardenable mixtures containing polyfunctional aromatic cyanic acid esters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4116946A (en) * 1976-06-24 1978-09-26 Bayer Aktiengesellschaft Hardenable mixtures containing polyfunctional aromatic cyanic acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0373784A3 (fr) * 1988-12-12 1992-01-22 Imperial Chemical Industries Plc Polymère aromatique

Also Published As

Publication number Publication date
FI880541L (fi) 1988-02-05
ES2005870A6 (es) 1989-04-01
KR880701258A (ko) 1988-07-26
JPH01501156A (ja) 1989-04-20
AU7396487A (en) 1988-01-11
DK60788D0 (da) 1988-02-05
DK60788A (da) 1988-02-05
CA1274045A (fr) 1990-09-11
US4665154A (en) 1987-05-12
AU592192B2 (en) 1990-01-04
EP0270601A1 (fr) 1988-06-15
FI880541A7 (fi) 1988-02-05
FI880541A0 (fi) 1988-02-05

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